Synthesis and comparing the antibacterial activities of pyrimidine derivatives

Andrews, Benjamin I.; Komathi, K; Mohan, S.

doi:10.1007/s12039-017-1228-z

Cited by 22 publications

(13 citation statements)

References 18 publications

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“…However, C5 esters reacted with hydrazine hydrate, in ethyl alcohol and in the presence of H 2 SO 4 , to give hydrazides [37,38] (Figure 1). The reaction of C5 esters with thiosemicarbazide, in acetone, to afford thiosemicarbazones is reported ( Figure 1) [39]. The latter data stimulate our interest to investigate the reactivity of C5 ester towards hydrazine hydrate under solvent-free conditions which produce three different ring cleavage products.…”

Section: Introductionmentioning

confidence: 87%

Solvent-Free Ring Cleavage Hydrazinolysis of Certain Biginelli Pyrimidines

Said

Eldehna

Ghabbour

et al. 2018

Journal of Chemistry

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Certain Biginelli pyrimidines with ester substitution in C5 were subjected to unexpected ring opening upon solvent-free reaction with hydrazine hydrate to give three products: pyrazole, arylidenehydrazines, and urea/thiourea, respectively. The nonisolable carbohydrazide intermediates are formed firstly followed by the intermolecular nucleophilic attack of terminal amino group of hydrazide function on sp2 C6 rather than the sp3 C4 to give the ring adduct which was produced as a final product.

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Section: Introductionmentioning

confidence: 87%

Solvent-Free Ring Cleavage Hydrazinolysis of Certain Biginelli Pyrimidines

Said

Eldehna

Ghabbour

et al. 2018

Journal of Chemistry

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“…Andrews et al 89 synthesized some new 2-amino-1,3,4-thiadiazole derivatives substituted at C-5 of thiadiazole ring with dihydropyrimidine moiety. The compounds such as 36 were evaluated for in vitro antibacterial activity at a concentration of 10 μg/mL by measuring the inhibition area on agar plates (diffusion method).…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

2-Amino-1,3,4-thiadiazole as a potential scaffold for promising antimicrobial agents

Şerban¹,

Stănăşel²,

Șerban³

et al. 2018

DDDT

150

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Pathogenic microorganisms are causative agents for different types of serious and even lethal infectious diseases. Despite advancements in medication, bacterial and fungal infections continue to be a growing problem in health care. As more and more bacteria become resistant to antibiotics used in therapy and an increasing number of invasive fungal species become resistant to current antifungal medications, there is considerable interest in the development of new compounds with antimicrobial activity. The compounds containing a heterocyclic ring play an important role among organic compounds with biological activity used as drugs in human and veterinary medicine or as insecticides and pesticides in agriculture. Thiadiazoles belong to the classes of nitrogen–sulfur heterocycles with extensive application as structural units of biologically active molecules and as useful intermediates in medicinal chemistry. The potency of the thiadiazole nucleus is demonstrated by the drugs currently used. 1,3,4-Thiadiazoles and some of their derivatives are extensively studied because of their broad spectrum of pharmacological activities. The aim of this review was to highlight the main antimicrobial properties exhibited by derivatives possessing 2-amino-1,3,4-thiadiazole moiety. Many of the reported 2-amino-1,3,4-thiadiazole derivatives can be considered as lead compounds for drug synthesis, and several of them have demonstrated higher antimicrobial activity in comparison to standard drugs. Furthermore, taking into account the reactivity of the amine group in the derivatization process, 2-amino-1,3,4-thiadiazole moiety may be a good scaffold for future pharmacologically active 1,3,4-thiadiazole derivatives.

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“…Furthermore, pyrimidine derivatives have numerous antimicrobial applications, such as antibacterial, anti-Toxoplasma, fungicidal and antimalarial applications. Figure 1 depicts the structures of some previously studied drug molecules containing pyrimidine rings [ 13 , 14 , 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

DFT, ADMET and Molecular Docking Investigations for the Antimicrobial Activity of 6,6′-Diamino-1,1′,3,3′-tetramethyl-5,5′-(4-chlorobenzylidene)bis[pyrimidine-2,4(1H,3H)-dione]

et al. 2022

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Heterocyclic compounds, including pyrimidine derivatives, exhibit a broad variety of biological and pharmacological activities. In this paper, a previously synthesized novel pyrimidine molecule is proposed, and its pharmaceutical properties are investigated. Computational techniques such as the density functional theory, ADMET evaluation, and molecular docking were applied to elucidate the chemical nature, drug likeness and antibacterial function of molecule. The viewpoint of quantum chemical computations revealed that the molecule was relatively stable and has a high electrophilic nature. The contour maps of HOMO-LUMO and molecular electrostatic potential were analyzed to illustrate the charge density distributions that could be associated with the biological activity. Natural bond orbital (NBO) analysis revealed details about the interaction between donor and acceptor within the bond. Drug likeness and ADMET analysis showed that the molecule possesses the agents of safety and the effective combination therapy as pharmaceutical drug. The antimicrobial activity was investigated using molecular docking. The investigated molecule demonstrated a high affinity for binding within the active sites of antibacterial and antimalarial proteins. The high affinity of the antibacterial protein was proved by its low binding energy (−7.97 kcal/mol) and a low inhibition constant value (1.43 µM). The formation of four conventional hydrogen bonds in ligand–protein interactions confirmed the high stability of the resulting complexes. When compared to known standard drugs, the studied molecule displayed a remarkable antimalarial activity, as indicated by higher binding affinity (B.E. −5.86 kcal/mol & Ki = 50.23 M). The pre-selected molecule could be presented as a promising drug candidate for the development of novel antimicrobial agents.

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Synthesis and comparing the antibacterial activities of pyrimidine derivatives

Cited by 22 publications

References 18 publications

Solvent-Free Ring Cleavage Hydrazinolysis of Certain Biginelli Pyrimidines

Solvent-Free Ring Cleavage Hydrazinolysis of Certain Biginelli Pyrimidines

2-Amino-1,3,4-thiadiazole as a potential scaffold for promising antimicrobial agents

DFT, ADMET and Molecular Docking Investigations for the Antimicrobial Activity of 6,6′-Diamino-1,1′,3,3′-tetramethyl-5,5′-(4-chlorobenzylidene)bis[pyrimidine-2,4(1H,3H)-dione]

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